O’Brien was educated in Dublin and later became a civil servant while also pursuing his writing career. He is most celebrated for his unusual novelAt Swim-Two-Birds, which, though it was first published in 1939, achieved fame only after its republication in 1960. At Swim-Two-Birds is a rich literary experiment that combines Irish folklore, heroic legend, humour, and poetry in a style replete with linguistic games; on its publication it garnered praise from, among others, the experimental Irish novelist James Joyce. O’Brien’s brilliant parody of Gaelic literature, An Béal Bocht (1941), was translated as The Poor Mouth in 1973. His novels The Hard Life (1961) and The Dalkey Archive (1964; adapted as a play, When the Saints Go Cycling In, performed 1965), though written on a smaller scale than his masterpiece, are thought equally amusing. Another novel, The Third Policeman (1967), is more sombre in tone. Under the pen name Myles na gCopaleen, O’Brien wrote a satirical column for the Irish Times that drew worldwide acclaim for its incisive humour and use of parody. His journalism was republished in several collections, most notably The Best of Myles (1968).

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